learn the rules so you can break them

a framework for development i’ve heard about a lot is - imitate the greats, then once your skillset is built up you’ll be able to get creative and find your own style. a good example of this is picasso, who most of us remember for his abstract works and cubism. originally though, picasso got really good at realistic painting before he started experimenting and getting more creative

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for example, here are two of his more realistic-looking “early works” (surprisingly, from when he was just a child)

left: “self-portrait,” 1896

right: “science and charity,” 1897

contrast those above to one of picasso’s most famous pieces, painted much later in his life, showcasing a much more abstract style

“guernica,” (1937)

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one way to think about this is - learn the basics / fundamentals, which then gives you the right (or just the ability) to experiment and find your style

picasso is a pretty grand example, but there are ways to apply this to most disciplines. i’m thinking about tech because that’s the field i’m in. if you’re a founder (or operator, or investor even), i think it’s generally a good idea to start by reading the widely-respected literature. this might include things like zero to one, the mom test, paul graham’s essays, etc

the important step comes afterwards, either:

  • read and interpret the concepts, try to figure out what resonates with you and what doesn’t, what might work and what valid, logical critiques you have with commonly-accepted frameworks for entrepreneurship
  • or even better, instead of thinking about them, apply these concepts to the startup you’re working on and reflect on the results. certain rules might break for certain industries. generic and prescriptive advice isn’t right 100% of the time

the danger comes from reading the literature and then blindly spouting it, without interpreting, critiquing, or applying it. this is where all of the tech groupthink memes come from - everyone reading the same paul graham essays and thinking in the same way, leading to frameworks / markets / founder backgrounds (even fashion choices) that are a bit too consensus. basically all you need to do is apply some critical thinking - which means question assumptions. i’m guilty myself of not always doing this (and i think many investors generally are as well)

one thing i was thinking about recently is the framework of “replicate your idols.” generally, it seems like a good way to get started on “learn the rules so you can break them.” it can also help you become more like your idols if that’s your goal. for example, if you’re evaluating whether you should use a meeting note-taker or not, you could ask yourself “would my favorite investor do this?” and make your decision accordingly. this could be good because - maybe your idol became who they are because of their personality, which trickles down to their decisions on little things like meeting note-takers. it could be bad too though - what if you’re only reading about behavior your idol adopted after they became successful? i think about the example below:

in a stark contrast to all of the productivity hacks, life-optimizers, biohackers, etc. - it came out that jeff bezos’ morning routine involved dead time:

“i like to putter”

of course, controversial stuff like this always goes viral on twitter

but i’ve always thought: was he “puttering” in the mornings while building amazon into what it is today? before he was a billionaire, before the company achieved widespread success? seems unlikely.

so in this example, if you’re a young and hungry startup founder, and you’re on the beginning of your entrepreneurial journey, it might be dangerous to read something like this and try to replicate it.

perhaps instead of trying to change your behavior too much, lean into your strengths and authenticity. you are who you are and that’s what makes you special. applying this to the field i’m in, this is probably true for a lot of legendary investors - your uniqueness is what makes you special, as my colleague derrick would put it.